Sweet Home Chicago
by acklevoy
Summary: AU 1940s Chicago. Sam Winchester - private detective - hasn't  seen his brother, hitman Dean, in five years. A recent string of murders  forces Sam to deal with mob bosses, rent boys and his own painful past.  Wincest/Destiel/basically everyone.
1. The Visitor

It was well past dawn. The sun had been drifting across the sky, with the glow and the girth of a smug hedonist, for hours now. Even so, it was having trouble bringing light to a certain dingy office that sat inconspicuously above a cheap Italian restaurant on Chicago's West Side. The windows of the office were barely translucent, the result of years of neglect, and the blinds were half-drawn.

The office was a tiny room with a door to the hall and another to a water closet so cramped that you couldn't close the door if you wanted to stand up to piss. There was a sagging couch in the corner, with threadbare armrests and no hint at what its original colouring had been. Like almost every other surface in the place, it was littered with boxes and piles of paper. The filing cabinet looked as though a couple of feral cats had used it as a playground: the drawers were piled to the brim and beyond with paper that was in no way filed. Sam Winchester, covered by a blanket of newspaper clippings and old photographs, lay sprawled over his desk and its chair, his knuckles just grazing the floor. The traffic outside wasn't enough to cover his snoring, but it was no surprise that a big man breathed heavily. Even lying down, you could tell that he was tall. His shoulders were broad with layers of muscle that had been built and toned by years of homeschooled combat training. His soft brow and relaxed mouth – though usually hardened when he was conscious enough to control it – showed a milder side to the giant, but one that seemed waning and in a few years might fade completely from existence.

That's what Chicago does to a man, especially a man in the business of dealing with crooks, cops and corpses.

There was a sudden knock, a sharp _rap rap rap_ on the pane of glass in the door that read 'Winchester Private Detective Agency'. Sam – the current Winchester private detective – jerked awake, rubbing drool from the corner of his mouth. He shook his head a couple of times to knock his brain into gear and his makeshift blanket to the floor, and glanced around his office. It wasn't exactly in a fit state to receive visitors.

There was a minute where Sam lingered in that place between sleeping and waking, but then the knock came again and he leapt into action. He cleared his leftover salad – dinner from the night before, a trade-off to his body for the amount of coffee he drank each day – into the wastepaper basket next to his desk, which was surprisingly empty in a room so full of trash. A stack of photographs littering the desk were swept back into their yellow envelope and stuffed into a drawer, right next to his Colt .38 revolver. A quick sniff of his shirt revealed that he could go another few hours without a shower. Sam hauled the boxes of papers off the chair in front of his desk and onto the sofa, and kicked some more boxes aside to make a path to the door. After a final once over, Sam smoothed his hair back out of his eyes.

Before he could reach out to let in his visitor, the knob was turned and the door was swept open to reveal a woman who was definitely not part of the local milieu. She was in her late forties, though clearly no one had taken the time to let her know. Dressed to the nines in a pea green ensemble meant for a much younger woman with narrower hips and a more modest bust, she was the perfect metaphor for Chicago's obsession with youth. By contrast, her hair, instead of being styled into a voluminous celebration of rollers (as was the fashion), was quite conservatively knotted beneath her hat.

She stopped short upon entering the room. Her confidence, betrayed at once for the pretence it was by the nervous grip she had on her pearl necklace, was weakened by the unexpected mess and the unexpected man before her. She glanced around the office with a wrinkle of disdain in the bridge of her nose.

"Excuse me," she drawled, her eyes passing judgment over the office's disarray. Her voice was deeper than Sam had expected, but its curt tone matched the primness of her outfit and her hair. "I need to see John Winchester. It's a private matter, quite urgent." She finally turned to look up at Sam, who cocked his head at the mention of that name. It had been a while since he had heard it.

"You're looking for my father?"

The woman frowned, a surprise to Sam who thought she was already doing so. Clearly that was just the first layer of a veritable treasure trove of disapproving looks.

"_You're_ Dean?"

If John's name had come unexpectedly to Sam, this one made his heart judder. He could feel all the moisture leave his mouth and a slight chill surge across his skin. He opened and shut his mouth a couple of times, trying to remember how to work his vocal chords.

"You… you know my brother?"

The woman clicked her tongue, an unmistakable sign of her thinning patience.

"I need to see your father. Tell him to call me the minute he gets in." She reached into her clutch purse (pea green), and drew out a card to hand to Sam.

He looked down. It was a business card, small and cream-coloured, stating in a cursive script: 'Annabelle Smith – Antiques and Curiosities', followed by a phone number. Annabelle Smith had already turned to leave but Sam grabbed her arm. She spun around, her face twisted into an expression of shocked disgust. She looked down at the hand gripping her forearm, and then back up at Sam. His eyes widened with the sudden realisation of what he was doing and he dropped his arm to his side.

"Sorry, but my father's dead. He died five years ago."

Annabelle's eyebrows shot up, but the look in her eyes showed that she was not surprised.

"Shot?"  
>"Heart attack."<p>

A cold laugh; not humourless, but thick with malice.  
>"He would have hated that. A poetic end though, I suppose. Taking away the bastard's last shred of dignity." She paused, thinking. "You're a little young to be a private investigator."<p>

Sam grimaced, but tried to pass it off as a smile. His hands were twitching, invested with a sudden urge to reach up and squeeze the self-righteousness right out of her. Not trusting himself to speak, lest he say something politeness dictated he shouldn't, Sam waited for her next thought to spring unedited from her garishly painted lips.

"A little young perhaps, but tall. I like that. And you're carrying on the family business. Your father may have been a son of a bitch, but he got results." Sam resisted the urge to laugh. Cussing didn't seem to come too naturally to Annabelle Smith. She chewed around swear words like they were an unfamiliar delicacy that she wasn't too sure she liked.

"Well, if you're the Winchester in charge, maybe you can help me. I'll pay handsomely, but I require utter discretion and a certain disregard for the law –though, if you are your father's son, there should be no problems there." She smiled smugly as though at a private joke. "I'll need you to come to my store. Tomorrow afternoon. I close at five o clock, so come then and we will discuss my situation and your fee. Not that they will, but if anyone asks, you are interested in acquiring a new desk, understand?"

Sam folded his arms over his chest. He was, in short, completely perplexed. His line of work usually led him to deal with the dirtbags of the city, and it had been a while since he'd come up against a woman with such a strong sense of self-entitlement. His curiosity won out though, and, instead of using some inventive and perfectly insulting new phrases he'd picked up last time he was at Balthazar's, Sam extended his hand to grasp Ms Smith's.

"Sam Winchester. Five o clock you said?"

She nodded, glanced once more around the office, disapproval oozing from her every pore, and left.

Sam rubbed his eyes, wondering exactly what he had gotten himself in to. Having taken a moment to recollect himself, he marched back around behind his desk and placed a call on the black telephone. It rang a few times before a voice at the other end answered with a gruff 'Yeah?'

"Bobby. You got a lunchbreak coming up? I've got a couple of questions that need answers. Just had a visit from an antiques dealer who knew John. Right. Roadhouse, fifteen? Thanks."

He reached into the drawer and retrieved his keys, glancing down at the revolver lying there. He always felt slightly vulnerable when he left the office without it, but it would not be a good idea to walk in to the Roadhouse with a gun. He shut the drawer with a determined bang and walked to the hatstand by the door. He pulled on his coat and slapped a brown fedora on his head. Slipping the business card into one of his oversized coat pockets, Sam tried to shake the ominous feeling that was stirring in his gut. His father's name, spoken out loud in that room for the first time in God knows how long, had done a little more than unsettle him. There was no ghost to haunt the old office, but Sam had never quite been able to exorcise the guilt.

He stepped into the hallway and locked the office door. He ran his fingers over the fading letters in 'Winchester' on the pane of glass, lingering on the 'W'. It was time to face some demons.

VVV

Sam walked the dozen or so blocks to the Roadhouse. It had been a speakeasy during prohibition days, but now it was the local dive bar for cops and two-bit crims alike. Ellen Harvelle ran it with an iron fist: the crooks knew better than to pull anything shady, and the cops knew better than to come to Ellen with the hopes of garnering more than a shot of whiskey or to chew more than the fat. She kept her mouth shut and the drinks flowing, and the Roadhouse was the place to go if you wanted nothing more than a place to muse and booze.

Sam swung open the door and breathed in the familiar scent of bourbon and cigar smoke. He walked past a table of men, smoking cheap cigarettes and talking in hushed tones. He recognised a few of them from various cases he'd worked in the past, but they were too engrossed in their conspiring to notice the PI. Ellen was cleaning glasses at the bar, looking older and more world-weary than she had the last time Sam had stopped by. Bobby Singer was sitting in a booth near the back, practically inhaling the peanuts sitting in front of him. His hair had been greying since Sam had known him, and his beard hadn't changed either in all that time. Off duty, he was dressed in his usual flannel shirt, today a red and blue number. An empty pint glass sat next to his peanuts.

Sam nodded to Ellen as he passed the bar. Two minutes later she brought him a coffee – black as sin – and another beer for Bobby.

"You boys wouldn't be up to anything that would cause discomfort to some of my less respectable patrons now, would you?" She looked meaningfully at the files spread out on the table.

"Relax, sweetheart. I bust crooks while I'm on the clock, not during happy hour."

Ellen smiled, her soft spot for the old inspector shining through.

"How's Jo?" asked Bobby, his tone changing to one of earnest sincerity.

"Your guess is as good as mine. She pops in maybe once a month. Says she's fine, but she doesn't tell me anything. That girl was out the door as soon as she turned twenty-one." Ellen turned to Sam. "It's good to see you, hun. I hope you're eating right. Here, why don't I whip you boys up a couple of my famous steak and kidney pies? Best in the state."

Running on nothing more than half a salad from the night before, Sam's stomach grumbled. Ellen laughed and walked back to the kitchen behind the bar.

"Now, what's this about an antiques dealer who knew your pop?"

Sam slid Annabelle's card out of his pocket and across the table. Bobby picked it up, squinting a little. He'd been John's police source back in the day, and he'd done more than his fair share of helping Sam since he'd taken over the family business. It was a two way street of course – Sam worked outside the law, and often slipped Bobby pieces of evidence that were obtained through less than legitimate means. Sam got a payday from grateful clients; Bobby got to put the perp behind bars.

It had always been more than that though, even when Sam was growing up. John might not have been the best father, but Bobby almost made up for it with his semi-regular swing-bys. These usually involved case files and beer for John and catchers' mitts and baseballs for the brothers.

"And you said she knew him? But she didn't know he's been _dead_ for five years?"

"Yeah, and she'd heard of Dean."

Bobby raised his eyebrows. He ran his fingers over the address on the back of the card then brought it up to his nose.

"Scented. Yeah, that description rings a bell. Never knew her name, but John mentioned a harpy a few times. I think he helped her bring a couple of questionable items into the country. This was before Balthazar was running the black market for the Outfit; she'd never get anything through these days without his say so. Musta been almost twenty years ago now. What do you think she wants?"

Sam furrowed his brow.

"Well, it seemed more like she was in some kind of trouble. I barely speak two words to her and she hires me? That's desperate, it's gotta be a sign of something big. She wouldn't come to John after twenty years just to move stock. For one thing, Bela wouldn't let it slide."

Bobby frowned in thought. He took a sip of beer, licked his lips and set down the glass.

"You're a good PI, Sam. Maybe even better than your old man. But this sounds like a shady deal. It might be too much for you. You've got your reasons for doing it I suppose. She didn't even give you a hint, _nothing_ about what she wanted?"

"Didn't pay me either, but I'm hoping that'll come tomorrow. As for why I did it… I don't know, Bobby. Something just made me want to see where it was heading." And she mentioned Dean, thought Sam. He wasn't used to hearing that name, not on anything but his own terms. That was really what had shocked him – possibly what had made him jump feet-first into a strange case. Not that he'd committed to working for Annabelle Smith, Sam reminded himself.

"If you ask me, it's about time you find your brother and hash all this family stuff out," gruffed Bobby, as though he'd been reading Sam's thoughts. "I'm guessing both of you have a lot of bottled up feelings about your old man, and it wouldn't hurt to get them out in the open for once. He was a good man when it came down to it. Now your pop never told me why you boys left, and I don't know why you haven't seen or spoken to Dean since the funeral, but whatever happened, it's time to deal with it. You clearly want to else you never would have taken this case. Find Dean. Talk to him, ya idjit."

A disingenuous smile flickered across Sam's visage. He finished his coffee in one gulp and stood up to go, just as Ellen brought out two steak and kidney pies.

"Oh no no no, you sit yourself down mister. And then we're going to talk about why it is you never come around anymore."

VVV

His belly full of pie, Sam sauntered out of the Roadhouse and into the glare of the midafternoon sun. Here, he was only a few blocks from the man who could tell him where to find his brother. Riding a wave of anxiety and uncertainty about where exactly the events of the day would lead, and doubting that he would enjoy the consequences, Sam made a snap decision and turned left instead of right.

He approached the street corner with mild trepidation. It was always risky to be seen in this part of town, as legal businesses were few and far between. Sam ought to know the dangers of loitering in such an area; more than a few jobs had seen him staking out this very street corner. Being the middle of the afternoon and nothing like peak hour, it was relatively safe from prying eyes. Besides, Sam was there on business, not pleasure. Either way, he pulled his coat collar high around his neck out of habit as he neared the group of half a dozen or so young men draped nonchalantly over the bus bench and in the doorways of the shops. There was thought behind each pose, creating a perfect tableau of perversion. It was a shame that not that many people were around to appreciate it. This was an easy shift, when the boys spent most of their time working on a tan rather than in the upstairs rooms.

Sam avoided eye contact and made a beeline for the boy with messy brown hair and piercingly blue eyes, who sat pride of place in the centre of the bench. Sam came up behind him and leant over (a fair way down considering his height), placing his lips next to the boy's ear.

"Castiel."

The boy twitched. He wasn't really a boy of course, but somewhere in his late twenties. He was the oldest on the street corner by far, but his lithe frame and infectious boyish grin had allowed him to remain in the profession that usually forced boys into retirement by the time they were of legal age to perform their services. There were notices up and down the street, threatening a $500 fine for public solicitation for prostitution, but the rent boys knew such deterrents were all but superfluous in a city like Chicago.

The man, Castiel, craned his neck to see Sam. When their eyes met, he smiled. Stoned again, thought Sam. No surprise there.

"Sam! It's good to see you." Castiel looked away mid-sentence, his gaze taking in the street but focusing on nothing. Sam rolled his eyes. He hated dealing with the rent boys, notoriously aloof if you weren't slipping money into their hand, but it was a necessary evil. They heard a lot, working the streets, and Castiel was the only one who knew where Dean would be.

"He's still in town?"

A beat, then Castiel nodded slowly.

"Where is he?"

This made the rent boy snap his head around to stare at Sam.

"You want to see him? You've never wanted to see him."

Sam thrust his balled fists into the pockets of his coat.

"Yeah, well, now I need to."

Need, not want. Castiel noted the difference.

"It's going to cost you."

Sam took his hands from his pockets and placed them on the back of the bench, either side of Castiel.

"He's my brother, Jimmy," hissed Sam. He stopped himself from adding, 'so stop being a little whore for two minutes and give me the fucking address.'

The other boys were attentive now; they stayed in their laidback poses, but all eyes were turned towards Sam. They'd long ago given up on trying to get Sam interested in what they were peddling, but they could still look.

Castiel stood. He walked around the bench and led Sam to the doorway of the building used by the boys when a customer did happen along. They climbed the rotting stairs, Sam having to take off his hat and bow his head the whole way (and even then hitting it on the broken light bulb). Castiel led the private detective into his room and shut the door.

"If you ever call me by my Christian name again," he sing-songed, as his smile took on the menacing quality of a shark, "I will slice you from your neck to your navel and make a nice scarf out of your intestines. Dean is staying at Bela's. And before you ask, no, I don't know why. Or where it is."

Sam held out a $50 note and Castiel pulled it slowly from his fingers without dropping eye contact.

"Like a good little whore," growled Sam, leaning forward to spit the words into Castiel's ear. The boy's smile withered into a glare, but the crisp note in his hand was Sam's safeguard against any real violence. You could bark all you wanted, but even Castiel knew not to bite the hand that fed you.

VVV

Sam's head was spinning as he stepped back out into the daylight. He felt sick, and it definitely wasn't from Ellen's steak and kidney pie. There were only a handful of reasons Dean would be staying with Bela, none of them good. Balthazar's daughter putting up a hitman would bode well for no one.

He ducked into the nearest bar and threw himself down on a stool, ordering a double. Mercenaries may seem somewhat redundant in a country rife with organised crime, but there were always men willing to pay to get rid of their problems, and most of them didn't want to be in debt to the mob. Dean travelled, usually only coming home to Chicago between jobs, preferring not to play in mobsters' backyards. If he didn't shack up with Castiel, he would be in a cheap motel somewhere on the outskirts of the city, far away from the Outfit. Staying with Bela was unheard of.

Sam's drink arrived and he downed it in two swallows, enjoying the burn of the liquor against the back of his throat. Two scenarios were playing out in his mind: in one, Dean was now working for Balthazar, which would land him in trouble further down the track; in the second, Dean needed Balthazar's protection, which meant he was in trouble _now_.

Whichever way you looked at it, Dean needed help. Sam had been hiding from his past for so long, but everything that had happened that day seemed to be pushing him to confront it. He ordered another double, knocking it back as quickly as he had the first, and made up his mind. Yes, it was time to face his demons. 


	2. All that Glitters

Sam stood a few feet back from the grave, trying to impress upon himself its significance as his father's final resting place. In reality it was nothing more than a ditch for the corpse to be thrown into and forgotten. Not that Sam minded. He was surprised at just how numb he felt looking at his father's lifeless body in a small wooden box. Three years hadn't made him hate him any less.

Sam scuffed his shoe. Not hate. Hatred was too strong a word. He was disinterested in his father's fate, still caught up in the resentment of his youth. Resentment, that was it. Otherwise known as the coldness that spread through Sam's entire body when John Winchester was mentioned. He would have loved to be able to call himself indifferent, but his past was too laden with painful memories to let any of his old anger dissipate. It was welded to his gut. He had been able to suppress it for much of the past three years, swept up in the bliss of a vagabond life with the man he loved, not having to answer to anyone, free from the hold of the man he was forced to call a father.

Sam had thought it would rear its head at the funeral, twisting his insides til his heart hurt. But he was numb. He preferred it that way.

Bobby was standing behind him somewhere with the other half a dozen people who had turned up. It had been good to see him again, someone from their father's life who actually made Sam smile. Bobby had come around quite often when Sam was younger. It wasn't just about cases back then. John would actually sit down with a beer and a friend and talk about something other than corruption. Sam wished he could remember more about those years. They'd serve him better than memories of the anguish that was to come later.

Next to him, standing a foot away with his hands thrust determinedly into his pockets, Dean was crying. It was the first time he'd had done so in God knew how many years. Two silent tears careened down his face, leaving traces like twisted scars across his cheeks. Sam knew that the hatred he had never felt (though guilt was another story) had burned fiercely within Dean through those three years on the road. He was just never sure whether Dean hated his father, or himself.

Sam had wanted to come to the funeral, despite the shit it was bound to stir up in the brothers' thoughts, because he thought it would be cathartic, liberating, to finally be able to let go. Dean would be able to break free from John's shadow and they could move forward, together. Sam was aching to reach out and grasp Dean's hand, to let him know with a single squeeze that he was there and that he always would be. He didn't, of course. Sam knew, even at a funeral, that it would be showing too much, especially for a stoic son of John Winchester. Besides, Dean had never been one for shows of affection.

Instead Sam turned from the grave and walked away. He didn't go too far – he had to wait for Dean to finish his goodbyes – but he couldn't just stand there any longer. He felt like an imposter. Funerals were meant to be a way for loved ones to say their farewells. Sam didn't belong among the people who would miss John Winchester.

A few minutes later, once the dirt was being shovelled back over John's coffin, Dean too stepped away. He didn't turn to Sam, but marched straight back to their car. He opened the driver's side door, got in, started the engine and drove away.

Sam didn't realise until it was too late, not until the sound of the engine – _his__favourite__sound__in__the__world_ – reached his ears. He began to race after the car, his tie flying out behind him and his shoes sinking in the damp grass of the cemetery.

"Dean! DEAN!"

Sam didn't know if Dean could hear him. If he did, he didn't slow down. He didn't stop. He didn't even look back.

That was five years ago.

Sam now stood across the street from a gaudy building with a paint job that hurt the eyes. The neon sign, a sinful red, flashed the words, _City__of__Angels_. Balthazar's club. There was no pretence. It was a strip joint, with poker tables in the back and another type of dealing in the bathrooms. The cops would raid it every couple of months so as to look like they were doing _something_ to fight organised crime in Chicago, but Balthazar's eyes and ears on the force let him know well in advance when to put the gambling and drug dealing on hold for a night.

It was knocking off time, which meant the street would soon be crawling with builders and businessmen alike. Each evening, rats from every corner of the city would flock to Balthazar's, seeking a little less loneliness or a little less clarity.

Sam crossed the street, barely checking for traffic. A few horns blared at him, braying like disgruntled goats, but he paid no attention. His blood was pumping a mixture of alcohol and adrenaline, and the edges of his vision and his mind were blurred. He saw the sign and he saw the door and he thought of his brother. That was the most his brain could handle, as thoughts of Dean Winchester left no room for trifling notions.

The goon on the door shot him a dirty look, no doubt trying to figure out why he knew Sam's face, but let him pass all the same. Sam breathed in deeply as he entered. The club had a distinct scent, slightly unpleasant at first, but one that would grow on you and come to be comforting in its familiarity. An interesting blend of booze, sex and money – the only thing that smelt similar was Balthazar himself.

The owner was sitting in a booth on a raised platform towards the back of the club, past the bar and the stages where half a dozen girls were already in full swing. Various villains and businessmen, including, Sam noted, Crowley McLeod, surrounded him. It would be so simple to just ask Balthazar if his daughter was planning on making an appearance that night, but Sam wouldn't even make it near the table before a goon would be in his path, telling him in no uncertain terms to get lost. The private detective and mobster had an uneasy truce, Balthazar recognising Sam as nothing more than a mild irritation who had on occasion proved somewhat useful. Definitely not on good enough terms for Sam to crash what appeared to be a serious business discussion.

He had always wondered how a Brit had come to hold such a prominent position in the Chicago Outfit, a force ruled and run by men of Italian stock, but there was no denying that he was a valuable asset to the mob. Balthazar Talbot had his fingers in almost every pie, but for the most part he ran the Outfit's import/export industry. He must have caught their attention during Prohibition, but rather than get rid of the competition, they'd recognised his talent and enlisted him. Balthazar was a born bootlegger, and now he ran the whole enterprise.

_City__of__Angels_, though, started in the 1920s and done nothing but flourish since then, was his pride and joy – a place where he could take care of business while indulging in a few of his favourite pastimes. While the Outfit didn't deal in narcotics, Balthazar did. It was a sign of his worth to the Outfit that they let him do so.

Taking one last glance at the cloud of cigar smoke rising from the booth, and wishing Bela's address wasn't one of the best-kept secrets in Chicago, Sam walked over to the bar. It was a dim room, but the atmosphere was ruined somewhat by the arrhythmic flashes of light from behind the stages. There was a small brass band squeezed into the corner of the place, providing a jazzy soundtrack to the high kicks and short skirts of the girls.

The place wasn't too full yet, and there was no one else seated on the bar stools. Older businessmen – some straight, some crooked, Sam observed – sat around the tables on the club floor while small lamps lit the ashtrays and red tablecloths and cast shadows on the men's faces. With no idea how long he would have to wait before Bela walked in the door, Sam sat with his back to the show and ordered a beer with the intention of pacing himself. It might take the whole night, but running into Bela was the only way he would be able to find Dean. He had barely drunk more than three sips though, when a hand was placed gently against his back and a soft voice spoke his name.

He turned to see a young woman with jet-black hair sit herself down on the stool next to his own. He looked down at her navy blue dress and furrowed his brow.

"Ruby. You're dressed."

The girl smiled smugly and smoothed out the fabric of her skirt.

"I just finished. Day shift. _But_, that doesn't mean I'm not working." She winked and drew a silk pouch from her stockings. "This is good stuff, Sam. It's never too late to get back in the game."

Sam turned back to his drink. He didn't want to be reminded of the mistakes he'd made in the year following John's death.

"Go home Ruby. I haven't touched that stuff, or you, in four years."

Her smile vanished. She tucked the purse back into her stockings and slid off the stool.

"Who says I'd let you touch me again? I know you've been going to see Castiel. God, is everyone in this city a fucking queer?" She spun around on her high heels and made for the exit. She'd almost reached it when Sam called after her.

"Ruby, hey! Do you know if Bela's coming in tonight?"

She just flicked up her middle finger and headed straight out the door.

Sam clicked his tongue in frustration, and, after a moment's consideration, ordered a whiskey neat.

VVV

Hours later, Sam found himself pressing Ruby up against the wall of his bedroom, her legs wrapped around his thighs and her moans filling his ears. Sam had his hands beneath Ruby's buttocks, his hips thrusting, pushing himself into her, almost violently. His eyes were shut; he couldn't tell if she was screaming with pleasure or in pain. He didn't care. The more she groaned the harder he pounded, her cries driving his momentum. There was a primal urgency in his movements, fuelled by the need to use her then never see her again. Each thrust slammed her harder against the wall, but the pain just seemed to build her ecstasy.

She lifted her chin so her mouth was on his ear, and struggled to whisper as he pounded the breath out of her, "I'd forgotten…how big you were."

Sam gritted his teeth. He wanted to strike her for dragging him back to reality, her voice sobering him and reminding him exactly whom he was fucking. Instead he slapped a hand over her mouth and sped the motion of his hips, shortening the time until the whole thing was over.

She let out a muffled cry beneath his hand and clutched his back, her fingernails leaving ugly red scratches as she climaxed. Sam didn't slow for her orgasm, didn't let her ride it out. He kept pushing until he reached his own –weak, a letdown after so much effort – then pulled away and let her fall to the floor. He dragged the navy blue dress off the bed and threw it at her, then went into his tiny bathroom and turned on the shower.

He felt dirty, contaminated by her. Stepping into the stream of hot water, he let it flatten his hair against his face. He pressed his cheek to the cold tile and grimaced as the water stung the scratches on his back. She had always been a mistake, and now Sam had one more thing to regret. He hated how much she knew of his past and how well she thought she knew _him_.

"Fuck!" Sam slammed his fist against the tiles. His head was spinning and he felt bile rising in his throat. He couldn't remember how much he'd had to drink – he couldn't even remember leaving the club – but it was the thought of what he'd just done and not the whiskey in his stomach and his bloodstream that was making him feel sick.

_Ruby_. _God__fucking__damnit._

He lifted his head and opened his mouth, letting the water from the showerhead run down his gullet. Four years. For four years he'd been clean of that 'emotional masochism', as Bobby had labelled it. A year of being that cliché – the depressed, drunken, damaged junkie who fucked strippers – before he'd gotten clean and taken over the agency. It may have just been sex, a drunken mistake brought on by loneliness or some sort of fucked up nostalgia, but to Sam it felt the equivalent of falling off the wagon and back into those dark days.

A few minutes later he exited the bathroom, feverishly rubbing a towel over his head to dry his hair. Ruby had gone. Sam muttered 'thank God' under his breath and fell back on to his bed. Just before dropping off to sleep, he tried to pinpoint the exact moment his day had turned to shit.

VVV

He was woken by the shrill ring of his telephone. The piercing tone cut through his dream – a hazy replay of the day's events – and sent a sharp pain shooting through his head. Sam groaned. He'd had more drinks than he could count, more than enough to make his head now feel like it was about to split open. He flung himself over to the telephone on the nightstand and picked up the receiver.

"Hello?"

"_Sam? You sound awful. Were you asleep? It's almost noon."_

Sam rubbed a hand over his face, trying to clear the sleep from his eyes. It took a minute, but eventually he realised who was on the other end.

"Bobby. Hey yeah, sleeping."

"_Wish__I__had__a__job__that__'__d__let__me__sleep__in__that__long.__I__just__wanted__to__let__you__know__that__I__dug__up__the__file__on__your__antiques__dealer,__but__that__can__wait.__I__take__it__you__haven__'__t__seen__the__paper__this__morning._"

Sam swallowed, willing his head to stop pounding with every breath. He was sluggish, but even with the ringing in his ears he was able to tell from Bobby's tone that something big had taken place overnight. Not that he was surprised; this was Chicago. The Windy City just seemed to be blowing in more trouble than usual for Sam Winchester. He took a deep breath.

"Who's dead this time?"


	3. Murder Most Foul

Sam was sitting in the diner down the road from his apartment, though it could have been any diner in the city. The décor was the same whatever burger joint you stepped in to: brightly coloured booths and stools with the walls painted a sickly pastel. It was just past lunchtime and most of the customers were finishing up their heart attacks waiting to happen and were on their way out.

A big mug of coffee sat steaming next to the newspaper on the table in front of Sam. The paper was open to the second page, a continuation of the headlining story. A young socialite had been found, naked, strangled to death in the back seat of her father's bottle green 1947 Cadillac convertible – at the bottom of Chicago Harbor. Anna Milton made the headlines often enough while she was alive; it was no surprise her murder had earned a three page spread.

Her father, Crowley McLeod, the man who owned all the sewers in Chicago, was equal parts politician and crook. It was common knowledge that it was Crowley who had single-handedly gotten the mayor elected, instead of taking the job himself. He was much too fond of the girls at Balthazar's and the lure of a poker table to give up his underworld associations for the sake of public appearance. The mayor may have been as crooked as a dog's hind leg, but on the face of things he was squeaky clean. Crowley McLeod would never have been able to live like that.

Sam shook his head. The Outfit may be an organisation of criminals, with a hand in any and every sort of felony, but at least they were upfront about it. A haze of thinly veiled corruption surrounded Chicago's politicians, and he hated the stench of it. It was tough living in a city where the 'good guys' had shadier agendas than the mob bosses.

He felt an odd sense of loss as he surveyed the photographs in the paper. He had barely known Anna Milton, and had often been put off by her wild child attitude, but he knew that her death would leave something of a void in the city.

Her story had a similar tone to her father's, but while Crowley occasionally drove a mile along the straight and narrow, she had long since veered into the side streets and back alleys of debauchery. The fiery redhead had set the standard for vivacious, troublesome daughters, tales of her escapades selling more papers than news of her father ever did. A different man on her arm each week; multiple arrests for drug possession (all hushed up and removed from her spotless record of course); the cause of half the car accidents in the city.

Sam had seen her plenty of times at _City of Angels_, sitting with Balthazar when she and Bela weren't turning heads with their manic laughter. Two heiresses to great empires, they were the city's favourite bad girls. There was no doubt about who had the upper hand in the relationship though: Bela was always leading her into trouble, and now Anna had ended up dead.

Sam lifted the mug of coffee to take a drink, blowing a little to cool it down before taking a sip. Just as the liquid reached his lips, a loud voice strolled through the door behind him, calling out 'Sammy!' A second later a rough hand clapped him on the back, jolting half of the coffee out of the cup and down his shirt. It splattered over the newspaper, causing the ink to run and turning the paper itself to a mush.

"Wow. Thanks Gabe. And _don't_ call me Sammy."

A grinning man, a head shorter than Sam and with the worst haircut the private detective had ever seen, sat down in the booth opposite. He looked down at the ruined paper and Sam's ruined suit and shrugged. His own suit was a sandy colour, and fit him like a potato sack. He was wearing a matching fedora, but even that was doing a terrible job at covering up his hair.

"Sorry. _Sam_. Don't worry about the paper; I brought you one from the office. Along with a few extra crime scene photos." He raised his eyebrows and tilted his head forward in that cocky way that he was prone to, throwing a yellow envelope onto the table. "These bad boys were too meaty to print. She was completely naked, you know." He winked, his laissez-faire disposition vexing Sam. "If you ask me, she was having too much of a good time in the back seat of her old man's Caddy, and the guy held on just a _little_ too long. There's a fine line between pleasure and pain. Trust me, almost took my own life a couple of times that way."

Sam's eyes widened in restrained shock and he looked quickly away from Gabe, mopping himself and the table with a handful of napkins. It was a fine line between pleasure and pain with Gabe as well – he was a well of information, being a photographer for the local newspaper, but his sense of humour and complete tactlessness often left a bad taste in Sam's mouth.

He opened the envelope and spread the photographs over the table. They were originals of the ones in the newspaper, plus a few shots of a more graphic nature that sent shivers down Sam's spine. Anna Milton had a body most men would kill to see, but a _dead _body did nothing except make him queasy.

As he was studying the photos, a waitress moseyed over and set a cheeseburger and strawberry milkshake down in front of Gabe. Sam leant back, the smell making his stomach protest. It was still in recovery from the night before.

"Did you even order?"

Gabe tilted his head back and dropped fries into his mouth.

"Di'n't need'o. I'm a wegular here."

"Why am I not surprised. It said in the paper that they found her clothes stashed under the seat. You got any photos of them?"

Gabe finished chewing and washed his fries down with a long slurp of his strawberry milkshake.

"Her _clothes_? Sweetheart, in case you didn't notice, she was _naked_. I wasn't gonna waste my film on a dripping wet dress and a pair of tights. The cops might bother with that sort of stuff, but journalists tend to go for shock factor."

Sam didn't reply. He just looked back to the photos, wearing a pensive frown. Gabe leaned forward, with his burger gripped in both hands.

"You okay, buddy? You seem a little – preoccupied."

Sam just shrugged. "I'm fine."

One thing about Gabe: as a journalist, he certainly had the incredulous look down. He ripped a mouthful from his burger and chewed slowly, waiting for Sam to admit that he wasn't, in fact, fine.

When the private detective refused to meet his eye, Gabe threw down the burger and flung both arms back over his seat. He was settling in for a long conversation.

"This wouldn't have anything to do with one Dean Winchester being back in town, would it?"

VVV

Sam walked back to his apartment for a change of clothes. He had a feeling Annabelle Smith wouldn't take kindly to a coffee-stained suit. He thought over everything Gabriel had said in the diner, about his brother being a no-good deadweight who would only cause for trouble for Sam. Hitmen tended to be somewhat emotionally unstable, if not completely devoid of emotion.

Dean certainly fitted that bill. Growing up with John Winchester wasn't likely to make an upstanding, mentally secure citizen of anyone. Sam was a lot more damaged than he liked to show. The brothers had found a way to cope though, together. Without him, Sam wasn't surprised Dean had turned into a contract killer. At least he was good at what he did. And what he did was kill people.

That didn't mean that Sam wasn't going to do his utmost to help his brother out of whatever trouble he had gotten himself into. It wasn't a choice; it wasn't a decision he had to make. It was the only option.

After climbing a few flights of stairs, Sam unlocked the front door of his apartment. There was a lingering scent of perfume, Ruby's perfume. Sam almost gagged on it, and hurried to open all the windows in the place. His apartment was barely more than one room, with not even a door between the bedroom and the kitchen/living area. Sam didn't need a lot of space. Most nights he fell asleep in his office anyway.

He fetched a fresh suit from his closet. It needed a bit of an iron but Sam didn't have time. He undid his tie and dropped his trousers. His jacket had escaped the spilt coffee, but it didn't match the clean pair of pants so it too had to go. He walked into the bathroom to splash some water on his face, and looked up at his reflection in the mirror.

He looked like shit. There were circles under his eyes and rough stubble covered his chin. His skin was sallow. He usually looked crap after a heavy night but this was something more. Sam could deal with work-related stress; it was the family stuff he wasn't so good with. This was five years of emotional turmoil manifesting to make him look like death.

_Emotional turmoil_. Sam let out a strained laugh. Some woman had said Dean's name and suddenly Sam was breaking apart. He hadn't seen him in five years. He wasn't any closer to seeing him now. Dean was a grown man, he could take care of himself. Did he really need to find him?

_Yes_. Another look in the mirror, at what the thought of Dean was doing to him, what it had made him do last night, and Sam knew that he'd postponed the inevitable long enough.

Then again, it would make sense to finish dealing with Annabelle Smith before he got into anything too heavy.

He took a razor from beneath the sink and sighed with something like pleasure at the feel of the cold metal against the skin of his jaw. Once he was presentable, he walked back to his bedroom and put on his clean suit. Before leaving, he reached under one of the pillows on his bed and withdrew a Colt revolver, this one a 45, and slipped it into the back of his waistband, covering it with his jacket. He doubted whether Annabelle Smith herself would pose a threat, but her demeanour in his office the day before had suggested that her situation could turn perilous.

He shut all the windows before leaving (the perfume scent barely noticeable now) and took stock of the contents of his fridge. He made a mental note to get more milk on the way home.

VVV

Sam pulled out of the garage in his maroon 1941 Lincoln Zephyr, a three seater with barely enough room for his legs. It was nothing like the black 1937 Chevy sedan he'd spent the best three years of his life in. Sam and Dean had made it work: driving across America, grifting when they could, thieving when they couldn't, nights spent in open fields under the stars, nights spent in the back seat.

His Lincoln didn't have a back seat.

The shop sat in the middle of a run of boutique stores, the green and gold lettering above the door reading _Smith Antiques_. Sam parked around the corner and sat in his car until ten past five, reading the newspaper Gabe had given him.

The murder of Anna Milton. This was a big deal, and could make a big case. It was a tragedy of course, but men like Sam who made a living out of tragedy weren't above a little exploitation if it meant publicity and a big payday.

He would wait a day before dropping in on Crowley. At the very least it wouldn't hurt to pay his condolences, and leave his card on the off chance that the businessman wasn't happy with the efforts of the boys in blue.

Having waited long enough, he got out of the car and walked to the shopfront. There was a burly man looking in the window of the tailor next door. The sign on _Smith Antiques_ said 'Closed' but Sam pushed and the door was unlocked. Annabelle Smith was inside, running a cloth along the edges of a hardwood table. She was wearing the same outfit as the day before, except in a pale mauve rather than the pea-green. She jumped as the bell jangled at the opening of the door. Seeing that it was Sam, she breathed deeply and clutched a hand to her chest.

"Mr Winchester. Yes. Come through to my office."

He followed her into a back room, a cosy office furnished with a mahogany desk with matching chairs and bookshelves. Sam didn't care much for her taste, but she at least had a sense of style. She sat behind the desk and motioned for Sam to take the one before it.

"Now I don't know how competent you may be, but I find myself in something of a dire situation. I have rushed into hiring you –"

"Sorry, but you haven't actually hired me until I've gotten a retainer."

Annabelle blinked a few times, and Sam waited for her brain to kick into gear.

"You want money. Of course. You'll have it, don't worry about that. But I think I should tell you my situation before we go any further.

"I have, of late, been involved in certain business arrangements that may not be entirely, ahem, legal."

Sam coughed into his fist, hiding a smile. "Almost twenty years ago, you were arrested for receiving stolen goods. I'm not here to judge you, and I'm not here to turn you into the police for whatever it is you've been doing. If I work for you, I work for you, so it's best to just tell me the truth. Now I don't exactly know what your relationship with my father was, but I think I can guess."

Annabelle smiled slowly, a conceited smirk that Sam was beginning to strongly dislike.

"We weren't sleeping together, if that's what you're implying."

At this, Sam laughed out loud. He didn't know much about his father, but he knew enough to find the thought of him and Annabelle Smith in any sort of romantic relationship completely absurd.

"Uh no, I didn't think you were." Annabelle's smirk dissolved. "Private detectives tend to run more on the wrong side of the law than the right side, so I'm assuming he had some hand in helping you move the stolen merchandise. Anyway, that's the past, and we're not here to talk about that."

And it was true. Sam realised, then and there, that he didn't want to know about his father's past. Growing up, everything is simple. Black or white. Good or evil. Right or wrong. But even at an early age, Sam had never been sure whether to cast his father in the role of hero or villain.

Ever since taking over as the Winchester private detective, he had started to see why. Private eyes blurred the lines between right and wrong, and a blurry glimpse of his father's morality was all Sam had ever gotten.

"Oh, he had some hand in it alright. He was also the one who turned me in to the police."

Or maybe he did want to know. No. Sam shook his head. He was there to take a case, and even though the mention of his father – and Dean – had helped nudge him into it, it didn't matter now. Sam twiddled his thumbs, the awkwardness in the air causing him to fidget.

"Right. Sorry about that. So… What can I help you with now? Dire situation, you said."

Annabelle rubbed her arms. She was oscillating between poise and panic, and the panic was starting to take over. She spoke quickly, wanting to get the whole thing over with.

"Well, to sum it all up: I've been financing the production of antique copies."

"Fakes. Forgeries."

She glared at Sam, spitting out her next words. "Yes. Forgeries. There were two men, Frankie Moretti and Jonah Walker, who were making the pieces. Last week, a few days apart, they were both killed. Strangled to death." She hiccoughed and ran her hands over her hair, her façade of confidence falling away completely.

Sam didn't speak for a moment. His mind was jarring, trying to process this information but too shocked to work properly.

"Strangled?" he finally choked out.

"God, I know. How awful! Who strangles people? Why not just shoot them like a normal person?" She was becoming hysterical now, her voice rising higher and higher in pitch and her hands grasped tightly to stop them from shaking.

"Ms Smith, you really should hire some sort of protection, if you think your life is in danger."

"Oh I've already done that. He was standing outside the shop, if you didn't see him. What I need from you is to find out who killed them, or who hired someone to kill them, and get them off the streets! I can't go to the police, not without admitting that I was dealing with those men. They're known criminals, it's too suspicious."

Sam's brain was working now, and going at warp speed. How many murders by strangling had there been in Chicago in the past few months, in the past few _years_? Not many, that was for sure. Now three in just over a week? There was no way these weren't connected. One other thing was for certain: Sam was going to take this case.

"Okay. I'll find out who strangled them. And hopefully get him arrested before he can pay you a visit. You're sure they were killed over this, though? Not something else?"

Annabelle shook her head. "They were working for me, but they didn't know about each other. It's too much of a coincidence for it to be about anything else. I have phone numbers and addresses for them both." She rummaged through her drawer and drew out her purse. She pulled out a handful of bank notes, and a few pieces of paper that she thrust into Sam's hands. "And your fee. I'm not sure what your usua-"

"It's a daily rate, with two days' pay upfront. What you're holding now looks about right."

Annabelle seemed a little reluctant, but handed over the wad of cash.

"You'll tell me as soon as you find anything?"

Sam stood. "Of course. I'll call here each day, just after five. If I find anything concrete I'll come in person. Just make sure that rhinoceros outside does his job properly."

He walked back through the shop and into the street. He nodded at the goon who just glared back at him, his hand inside his coat.

Sam stalked to his car, his gaze on the sidewalk, trying not to think about how the turn of the tide was slowly dragging him out of his depth.


End file.
